Source: James Pankow plays trombone, Ray Hermann plays sax and Lee Loughnane plays the trumpet as the band Chicago perform during a concert at Arena Monterrey on May 27, 2025 in Monterrey, Mexico. (Medios y Media/Getty Images)Chicago Setlist: ‘The Windy Cities Tour’Chicago is hitting the road with Styx for The Windy Cities Tour, bringing two midwestern classic rock heavyweights together for one of the biggest tours of the summer. RELATED | Styx Setlist: ‘The Windy Cities Tour’The tour marks the first time Chicago and Styx have co-headlined a full run together, with both bands playing sets packed with decades of hits. Chicago’s setlist has remained fairly consistent throughout the tour, giving fans a good idea of what they can expect to hear when the band comes to their city. RELATED | Walter Parazaider, Founding Member of Chicago, Dead at 81Here’s a look at the songs Chicago has been playing on The Windy Cities Tour.